"Sing With Me" shows how Carlisle Jacobson, a recent college graduate beginning a teaching career in the Washington, D.C., area in 1998, realizes he's learning as much as he is teaching. Carlisle brings to his work a belief that every student must, without a doubt have opportunities to achieve anything they imagine, but before long he's learning, through personal experiences, that many young people don't have the advantages he enjoyed as a child of privileged and wealthy society in the horse country of Virginia, only a day-trip away from Washington but worlds away from its streets plagued by crime and nearly cut off from hope. And while Carlisle has enjoyed hunting since he was young, he discovers firearms are used frequently in D.C. for hunting down other people, with innocent bystanders shot as frequently as the hunters' intended targets. His most frequent teacher in learning that he has a lot to learn is Lucia Sanspeur, a woman unlike any he's known and anyone he ever expected to meet. Lucia doesn't mince words and makes clear her ideas, every one of which he hangs on in rapt attention. Her voice captivates Carlisle from their first encounter, and almost as quickly her ideas propel him toward understanding that, even as he professes concern and empathy for his students and for her, he looks at the world and other people through a sense of wealth and privilege. The primary tenet of Carlisle's perspective, which he acknowledges but tenaciously wrestles to accept, is that as a white man he should exert control over and receive respect from all other people, particularly blacks and other minorities. Lucia, as a black woman, makes vividly clear the problems with his perception. Carlisle's rapid education in learning about life moves into advanced studies and his stumbling journey toward accepting the basic prejudices in his regard for other people nearly tumbles to a complete stop when he experiences first-hand the violence and crime that victimize many people in the area daily.